1-Phenyl-6-<(tetrahydro-2H-pyran-2-yl)oxy>-1-hexyn-3-ol | 190258-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 1-Phenyl-6-<(tetrahydro-2H-pyran-2-yl)oxy>-1-hexyn-3-ol
• 英文别名: 1-phenyl-6-((tetrahydro-2H-pyran-2-yl)oxy)hex-1-yn-3-ol；6-(Oxan-2-yloxy)-1-phenylhex-1-yn-3-ol
• CAS: 190258-39-0
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: KBXRGPCZRNWISW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Phenyl-6-<(tetrahydro-2H-pyran-2-yl)oxy>-1-hexyn-3-ol 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 碘 、 六正丁基二锡 、 三乙胺 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 5.0h， 生成 (E)-2-benzylidenecyclopentan-1-ol
  参考文献：
  名称：

  乙烯基的立体选择性氢转移反应：通过氢化硅的单分子链转移使炔基碘化物环化

  摘要：

  取决于所用的前体和自由基链的类型，几种取代的己炔基碘和庚炔基碘化物的环化立体选择性地进行，以得到E-或Z-环外双键。在单分子链转移（UMCT）反应中，中间乙烯基基团对氢的分子内提取仅导致E-异构体，而传统的氢化锡方法通常为Z-异构体提供良好的选择性。

  DOI：

  10.1016/s0040-4020(97)00257-3
• 作为产物：
  描述：

  4-四氢吡喃基氧基-丁烷-1-醇 在 正丁基锂 、 草酰氯 、 二甲基亚砜 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 1-Phenyl-6-<(tetrahydro-2H-pyran-2-yl)oxy>-1-hexyn-3-ol
  参考文献：
  名称：

  Au-catalyzed intramolecular hydroalkoxylation of gem-difluorinated alkynols

  摘要：

  The intramolecular hydroalkoxylation of gem-difluorinated alkynols was found possible under Au catalysis, allowing for the preparation of a series of fluorinated heterocycles. The nature of the solvent was found to be especially critical in the cyclization of gem-difluorohomopropargylic alcohols as it dictated whether the resulting 2,3-dihydrofuran underwent subsequent aromatization to the corresponding furan or not.

  DOI：

  10.1016/j.jfluchem.2018.09.009

文献信息

• Formation of Angularly-Fused Triquinanes by Successive Use of the Pauson-Khand Reaction and Radical Closure
  作者：Derrick L. J. Clive、Derek C. Cole、Yong Tao

  DOI：10.1021/jo00085a032

  日期：1994.3

  Angularly-fused triquinanes (see Table 1) are accessible by sequential use of the Pauson-Khand reaction and radical cyclization. The Pauson-Khand step works in the presence of homolyzable bonds, such as C-Br and C-SePh. The method seems best suited to the preparation of triquinanes containing heteroatoms, as the starting materials are then easily made. In one case the radical closure step (15 --> 16 and 17) generated two five-membered rings fused in a trans manner; this stereochemistry was confirmed by X-ray analysis of the crystalline product.
• Clive Derrick L. J., Cole Derek C., Tao Yong, J. Org. Chem, 59 (1994) N 6, S 1396-1406
  作者：Clive Derrick L. J., Cole Derek C., Tao Yong

  DOI：——

  日期：——
• Au-catalyzed intramolecular hydroalkoxylation of gem-difluorinated alkynols
  作者：Jean-Denys Hamel、Jean-François Paquin

  DOI：10.1016/j.jfluchem.2018.09.009

  日期：2018.12

  The intramolecular hydroalkoxylation of gem-difluorinated alkynols was found possible under Au catalysis, allowing for the preparation of a series of fluorinated heterocycles. The nature of the solvent was found to be especially critical in the cyclization of gem-difluorohomopropargylic alcohols as it dictated whether the resulting 2,3-dihydrofuran underwent subsequent aromatization to the corresponding furan or not.
• Stereoselective hydrogen transfer reactions of vinyl radicals: Cyclization of alkynyl iodides by Unimolecular Chain Transfer from silicon hydrides
  作者：Angeles Martinez-Grau、Dennis P. Curran

  DOI：10.1016/s0040-4020(97)00257-3

  日期：1997.4

  hexynyl and heptynyl iodides proceeds stereoselectively to give either E- or Z-exocyclic double bonds depending on the type of precursor and radical chain used. In UniMolecular Chain Transfer (UMCT) reactions, the intramolecular abstraction of hydrogen by the intermediate vinyl radical leads exclusively to the E-isomer while the traditional tin hydride method usually provides the Z-isomer with good

  取决于所用的前体和自由基链的类型，几种取代的己炔基碘和庚炔基碘化物的环化立体选择性地进行，以得到E-或Z-环外双键。在单分子链转移（UMCT）反应中，中间乙烯基基团对氢的分子内提取仅导致E-异构体，而传统的氢化锡方法通常为Z-异构体提供良好的选择性。